Green synthesis of xylan hemicellulose esters

The esterification of xylan type hemicelluloses, isolated from birchwood, was carried out firstly in homogeneous conditions using N,N-dimethylformamide (DMF) and lithium chloride (LiCl) in the presence of 4-dimethylaminipyridine (DMAP). The degree of substitution (DS) of xylan acetates ranged between 0.9 and 2.0 as a function of experimental conditions. Due to the problems of toxicity and recycling of DMF, an alternative method of esterification is reported in the second part of this work, performing in the absence of organic solvent and using DMAP or methanesulfonic acid (MSA) as catalysts. Acetylation reaction catalyzed by MSA was developed through an experimental design in order to achieve the highest DS under the mildest conditions. The significant factors and their interactions were identified. The optimization of reaction parameters allowed to obtain a high DS (1.6) and maximal yield (85%). Moreover, the reactivity of propionic and hexanoic anhydrides was evaluated and hydrophobic xylan esters with low degrees of substitution were obtained.

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► Green synthesis of xylan esters is developed.
► The reactivity of acetic, propionic, and hexanoic anhydrides is evaluated.
► Xylan acetates with high degree of substitution are achieved.
► The experimental design is used to study systematically the effect of different parameters.